- This popular moment, doubles as Crowning Moment of Awesome:
Principal: Mr. Madison, what you've just said is one of the most insanely idiotic things I have ever heard. At no point in your rambling, incoherent response were you even close to anything that could be considered a rational thought. Everyone in this room is now dumber for having listened to it. I award you no points, and may God have mercy on your soul.
- Billy's reaction to "The Puppy Who Lost His Way".
Billy (after Ms. Lippy finishes the story)
: Whoa whoa whoa, Ms. Lippy. The only part of the story I
didn't like is that the little boy gave up looking for Happy after only an hour
. He didn't put up posters or anything. He just sat on the porch like a goon and waited. That little boy's got to think
; you've got a pet. You've got a responsibility. When your puppy is lost, you don't just look for an hour and then call it quits. You get your ass out there and you find that fucking dog! Ms. Lippy (dumbstruck)
: I... think it's time to play dodgeball.
- All while the kids are sleeping.
- The cursive writing scene. Billy writes a couple of words and thinks he's pretty hot shit compared to the (other) kids in his class, but then he is tasked in writing a words with "z"s in it. His suffering as he attempts to improvise/recollect what a z looks like in cursive looks pretty real.
Miss Vaughn: "Rirruto?"
Billy: ...Those are Zs.
Miss Vaughn: They look like Rs to me.
Billy: That's not fair; Rizzuto isn't a word, he's a baseball player! You're cheating!
Billy: <sulking> I hate cursive and I hate all of you! I'm never coming back to school, NEVER!! <runs>
- From the Deleted Scenes: "I'm Horny!"
- The ending where everyone, even the periphery characters like the disgusting lunch lady, the bus driver, and the not so imaginary penguin all start kissing each other.
- The dodgeball scene.
Billy: Now you're all in big, big trouble.
- Billy's confrontation with the older O'Doyle kid:
[Threatening] O'Doyle, I got a feeling your whole family is goin' down ... [Cheerfully] but right now, I gotta study!
- "BILLY PASSED THE THIRD GRADE! OH WHAT A GLORIOUS DAY-AY! OH, PASSING THE THIRD GRADE, THE BILLY MADISON WAY-AY!"
- How much the bus driver gets ticked off by a sandwich to the head.
Kid: I dare you to throw your lunch at the bus driver. (Other kid throws lunch at the bus driver)
Bus Driver: (yelling back at the kids) HEEY! (Swerves through traffic before regaining control as children giggle)
Veronica: Who threw that?
Bus Driver: I'll turn this damn bus around! That'll end your precious little field trip pretty damn quick, won't it? Little shit!
- Made funnier with a lingering shot on the bus driver turning increasingly red and tear-eyed.
- The bus driver played by Chris Farley going on about how hot Veronica Vaughn is. Adam Sandler is visibly struggling to not laugh.
Bus Driver: That Veronica Vaughn is one piece of aysh. I know from experience, dude. You know what I mean?
Billy: No, you don't...
No, not me personally, but a guy I know, him and her Got. It. On.
Billy: No, they didn't.
Bus Driver: No, no they didn't. But you can imagine what it'd be like if they did, right? (nudging) Huh, huh?
(Billy pats his shoulder and boards the bus)
- "Everybody in? Good. Great. Grand. Wonderful. (Door closes) NO YELLING ON THE BUS!!!!!!"
- The bus driver, Frank and Jack stealing all the third graders' lunches with the bus driver laughing as he's scarfing them down.
- Billy's reaction to a classmate having peed his pants, a loud-as-possible "GYOO!!!"
- Turns into a Crowning Moment of Heartwarming as well since he puts water on his crotch and claims that peeing your pants is cool when you're a grownup to help him save face.
- "If peeing your pants is cool, consider me Miles Davis."
- Billy visits his 3rd grade friends after getting bullied at high school. When one chubby kid says he can't wait for high school, Billy says this:
Don't you say that. Don't you ever say that. Stay here. Stay here as long as you can. (Grabs kid by the face and shakes him violently) For the love of God, cherish it. You have to cherish it.
- "Man, I'm glad I called THAT guy."
- The Principal at Knibb High and his weird and very public obsession with his wife cheating on him.
- The entirety of the Big Lipped Alligator Moment song in the middle of the movie qualifies. Particular moments include the obvious dubbing of Sandler's voice, Veronica randomly dressing as a German fraulein and talking about her "nice rack," the song ending with everyone asking one another if they "HAVE ANY MORE GUM MORE GUM MORE GUM," and the clown on stilts who fell over several scenes ago suddenly reappearing, getting up off the ground, and cheerfully singing directly to the audience:
Clown: Hey, kids, it's me! I betcha thought that I was dead! But when I fell over, I just broke my leg and got a hemorrhage in my head!
- Upon hearing the press conference from the elementary school principal and the reporter mentions that the 27-year old Billy bribed and cheated his way to passing through to middle school:
Billy's friend Frank, played by Norm Macdonald: "Now hold on, maybe it's somebody else."
- Max Anderson has the NBC chimes for his doorbell.